Acetone → HCID 57576736, compound

HRID 599450Notes

Reaction equation

HRID 599450 reaction equation
[NH2:1][O:2][CH2:3][C:4]1[N:5]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:6]2[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[N:9]=[C:8]([NH2:16])[C:7]=2[N:17]=1.[CH3:22][C:23]([CH3:25])=O>CO.C(#N)C>[NH2:16][C:8]1[C:7]2[N:17]=[C:4]([CH2:3][O:2][N:1]=[C:23]([CH3:25])[CH3:22])[N:5]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:6]=2[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[N:9]=1

Participants

5

Reactant 2

HCID 180AcetoneHCID 11289248HCID 11289248, compound

Product 1

HCID 57576736HCID 57576736, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 2-[(aminooxy)methyl]-1-(2-methylpropyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine (700 mg, 2.42 mmol) in methanol (12 mL) and acetone (12 mL) was stirred at room temperature for 1 day, then was concentrated under reduced pressure to yield an oil. The oil was diluted with acetonitrile and concentrated under reduced pressure to yield a solid that was recrystallized from acetonitrile. The crystals were isolated by filtration, washed with acetonitrile, and dried in a vacuum oven to yield 379 mg of acetone O-{[4-amino-1-(2-methylpropyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-2-yl]methyl}oxime as white crystals, mp 176-177° C.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customto yield an oil
  3. concentrationconcentrated under reduced pressure
  4. customto yield a solid
  5. customthat was recrystallized from acetonitrile
  6. customThe crystals were isolated by filtration
  7. washwashed with acetonitrile
  8. customdried in a vacuum oven

Sources & evidence

ORD record
ord-11ef98691f78486bb12ec918bd3f9abc
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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